At the end of Chicago PD Season 8, Upton proposed to Halstead. ... She's deeply affected by her actions, and it led to her deciding to tell Halstead exactly how she feels about him. She loves him, but what we didn't expect was for her to pop the question.

Does Halstead have feelings for Upton?

Upon arriving back at her apartment following the ordeal with Voight and the suspect responsible for shooting Burgess, Upton tells Halstead she loves him before suggesting they take their relationship to the next level in asking him to marry her.

Are Jay and Upton together?

Fans ready to watch Chicago P.D. Season 9 can't wait to see how Jay Halstead and Hailey Upton's relationship progresses on the show. At the end of the Chicago P.D. Season 8 finale, Upton proposes to Jay, leaving him speechless and shocked.